JP2646421B2 - Obesity prevention agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a prophylactic agent for obesity containing glycolipids obtained from oilseed as an active ingredient.

[0002]

2. Description of the Related Art In order to produce oils and fats from oil seeds such as soybeans, rapeseed, sesame, etc., usually, the seeds are squeezed and / or extracted with an organic solvent such as hexane to obtain crude oil, which is stored. Leave it in a tank to precipitate a precipitate, or so-called ori, or blow water or steam to hydrate and agglomerate the gum.After separating them, purify, if necessary, deacidification, decolorization, deodorization, etc. The product is treated as an oil and fat product.

[0003] Here, the gum substance is also called a soapstock, and generally comprises 50 to 80% by weight of water and 20 to 50% by weight of an oil component. Among these, the oil component includes neutral lipids and fatty acids containing triglyceride as a main component and lecithin. And phospholipids and glycolipids commonly referred to as Such gums are removed from water to form a paste-like lecithin, which is then concentrated using a solvent such as acetone or ethanol, or the individual components thereof such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, etc. are highly concentrated. It is purified to a high degree of purity and used as an emulsifier in the fields of food, cosmetics, agricultural chemicals, pharmaceuticals and the like. In addition, the glycerides and fatty acids separated at this time are also reused in oil and fat related products. However, components based on glycolipids such as steryl glycosides and acylated steryl glycosides have not yet been found for industrial use or use.
It has not been used effectively.

[0004] On the other hand, in the process of producing sesame oil, for example, ori, which is a precipitate that precipitates when crude oil is allowed to stand, is usually used.
Separated from sesame oil and disposed of. It is known that the ori contains glycolipids mainly containing steryl glycosides and acylated products thereof.

[0005] By the way, the obesity phenomenon in organisms is generally caused by excess calorie intake, except for genetic or pathological ones, and accumulates body fat, causing not only the specificity of its appearance but also various plagues. It is feared that it may cause it. For example, Gordon et al., Ann. Inter
According to n. Med., 87, 393-397, 1977, it is suggested that obesity induces diabetes and heart disease. For this reason, various research and development have been promoted not only to treat obesity but also to prevent it in advance, but still effective measures, especially from the aspect of obesity prevention,
At present, no method has been found.

[0006] That is, most of the conventional methods for preventing obesity are based on dietary restrictions that limit the calorie intake, but this is accompanied by mental difficulty and is difficult to carry out. Or risk of pathological symptoms such as anorexia nervosa. Also,
Although obesity can be prevented by drug administration, side effects as well as efficacy must be taken into consideration, and it is difficult to say that a method that can be used easily and simply at the individual level to prevent obesity is used.

[0007]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a prophylactic agent for obesity which utilizes general-purpose oilseed components, does not involve dietary restrictions, has no concern about side effects, and can be used easily. Is to do.

[0008]

Means for Solving the Problems With respect to the above object, the present inventors have intensively studied the relationship between various components in oilseed and the effect of preventing obesity, and have completed the present invention.
That is, the present invention is an anti-obesity agent comprising a glycolipid as an active ingredient, which is obtained by fractionating gum or odor generated in a step of producing an oil or fat from oil seeds with a lower alcohol.

The oilseed used as a starting material in the present invention is a general-purpose raw material for producing oils and fats such as soybeans, rapeseed, corn, sesame, cottonseed, sunflower, safflower, flax, and palm. preferable. Regardless of whether or not the oil seed is roasted, squeezing and / or solvent extraction is performed to produce a crude oil, which is allowed to stand at, for example, 20 to 50 ° C. for 2 to 10 days, and deposits are formed. Alternatively, when water or steam is blown into the crude oil in an amount of 1 to 10% by weight, the gums coagulate and precipitate. Then, in the present invention,
The active ingredient in the present invention is fractionated and concentrated from the gum substance or the waste.

In the case of using the gum substance, first, water is removed therefrom using a suitable drying means, and neutral lipids, fatty acids, coloring substances and glycerides such as triglyceride and diglyceride are added to a ketone organic solvent such as acetone. The odorous components and the like are dissolved and separated to obtain a precipitate of polar lipids mainly comprising lecithin as insolubles. The precipitate contains lecithin composed of phospholipids such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidic acid, and lyso-form thereof, and the glycolipid according to the present invention.

Next, the dried product of the polar lipid is dissolved in, for example, hexane to obtain a silica gel column (Wako gel C-100).
First, the lecithin component is eluted using hexane as an eluting solvent, and then the glycolipid component is eluted using a lower alcohol such as methanol or ethanol as an eluting solvent. The glycolipid fraction obtained here is sitosterol,
Campesterol, oilseeds such as stigmasterol
Derived sterols and saccharides derived from oilseed such as glucose, galactose, stachyose, raffinose and the like, and acylated products thereof, that is, the hydroxyl group at the 6-position of the sugar chain and palmitic acid, oleic acid, and linoleic acid And the like as the main component. If necessary, the glycolipid fraction was dissolved in the new lower alcohol, and subjected to the same silica gel column chromatography again, whereby the acylated steryl glycoside was further concentrated, and the free steryl glycoside was further concentrated. Can be further divided into more concentrated sections.

When using the above-mentioned orifice, it is dispersed in, for example, hexane to separate a hexane-insoluble fraction from which neutral lipids and the like have been removed, and then dispersed in a lower alcohol to obtain a soluble fraction. / Lower alcohol =
Disperse or dissolve in 1/9 to 9/1 and fractionate to obtain a soluble fraction of lower alcohol, or disperse in lower alcohol to obtain a soluble fraction, and remove lower alcohol from any of these to make glycolipid the main component. Can be obtained. Here, the lower alcohol is preferably methanol or ethanol from the viewpoint of solubility, and if necessary, the fractionation operation can be heated to 40 to 50 ° C. and then cooled to increase the fractionation efficiency.

The glycolipid fraction thus obtained is obtained by repeating the above-mentioned solvent separation using a lower alcohol, or dissolving it in a lower alcohol and subjecting it to silica gel column chromatography as in the case of using gum. , Other ori components and free steryl glycoside enriched fractions.

In the present invention, an obesity preventive agent comprising the glycolipid fractionated as described above as an active ingredient is developed. That is, a glycolipid fraction containing at least 0.1% by weight or more of steryl glycoside and / or an acylated product thereof, or a concentrate of each glycolipid alone or added to a known food material is used for eating and drinking. It can be used as an animal feed or as a pharmaceutical preparation together with ingredients and carriers suitable for pharmaceutical use. Here, when the glycolipid component in the fraction to be blended is less than 0.1% by weight, a large amount of the fraction must be blended in order to exert the obesity prevention effect aimed at by the present invention. In addition, other components mixed at that time may suppress the effect of the present invention.

The agent for preventing obesity according to the present invention is preferably used in foods and drinks and animal feeds in a fraction containing glycolipids or a concentrate of each glycolipid in an amount of about 0.5 to 10% by weight, and A sufficient effect can be obtained by adding about 0.05 to 5% by weight of the lyl glycoside and / or acylated product. As a pharmaceutical preparation, known binders, excipients, and the like can be added orally in the form of powders, granules, tablets or capsules by ordinary methods, or can be taken orally, or can be used as usual stabilizers and auxiliaries. It can also be administered parenterally without injections. In this case, the blending amount of the glycolipid-containing fraction or concentrate according to the present invention is about 0.1 to 50% by weight, and 0.1 to 10% by weight of steryl glycoside and / or its acylated product.
% By weight. The dose can be appropriately changed depending on the condition, but is about 10 to 100 mg / kg / day.

[0016]

EXAMPLES In the following Reference Examples and Examples,% is based on weight. [Reference Example 1 Preparation of soybean lecithin and glycolipid fractions] The gum generated in the degumming step of crude oil obtained by extracting hexane from soybeans was dried, and 10 kg of acetone was added to 1 kg of the dried product. After stirring, the precipitate was collected and acetone was distilled off under reduced pressure to obtain 800 g of acetone-insoluble matter. Then, 600 g of this acetone-insoluble matter was dissolved in 7 liters of hexane, and the mixture was dissolved in a silica gel column (Wako gel C-100, 1.2 g).
kg), and 2 liters of hexane was flowed to collect elution fractions, and the solvent was distilled off under reduced pressure to obtain a lecithin fraction F1. Further flow 10 liters of ethanol to collect the elution fraction,
The solvent was distilled off under reduced pressure to obtain glycolipid fraction F2. The yields of F1 and F2 were 540 g and 55 g, respectively. When the composition of F1 was analyzed by high performance liquid chromatography, it was found that 30% of phosphatidylcholine, 26% of phosphatidylethanolamine and 16% of phosphatidylinositol were the main components, and the composition of F2 was analyzed by high performance liquid chromatography. , Steryl glycoside 14%, acylated steryl glycoside 40%, and other 46%.

500 g of F1 was dispersed in 10 volumes of ethanol and fractionated into an ethanol-soluble section and an ethanol-insoluble section. The yield after distilling off the solvent was 150 g of the ethanol-soluble fraction (F1-1) and 350 g of the ethanol-insoluble fraction (F1-2). When the respective compositions were analyzed, F1-1 was found to be phosphatidylethanolamine. 2
F1-2 was a lecithin concentrate containing 6% and phosphatidylinositol as a main component, and F1-2 was a lecithin concentrate containing phosphatidylcholine as a main component at 57%.

On the other hand, 50 g of the above F2 was
0 ml and dissolved in a silica gel column (Wako gel C-100, 1
kg), and flowed with ethanol, and then 2 liters of the first elution section (F2-1) and 2 liters of the subsequent elution section (F2-
2) Then, 2 liters (F2-3) of the subsequent elution fraction were collected. The solvent was distilled off from each section, the yield was determined, and composition analysis was performed. As a result, F2-1 was a glycolipid concentrate having a yield of 30 g and an acylated steryl glycoside of 88% as a main component. The yield was 18 g, which was a glycolipid concentrate containing 92% of free steryl glycoside as a main component.

[Example 1] Male SD rats 7 weeks old 4 weeks old
The animals were grouped as one group, a soybean oil-added group containing 10% soybean oil was replaced with a control group, and 5% of this soybean oil was replaced with the same amount of the other components shown below, and each group was a test group. Lecithin fraction added section: Lecithin fraction F1 described in Reference Example 1, glycolipid fraction added section: Glycolipid fraction F2 described in Reference Example 1, lecithin concentrate (1) added section: Reference Ethanol-soluble section F1-1 described in Example 1, lecithin concentrate (2) added section: ethanol-insoluble section F1-2 described in Reference Example 1. Table 1 shows the feed composition of each test plot.

[0020]

[Table 1] Note 1) Vitamin mix and mineral mix: AIN-762 manufactured by CLEA Japan, Inc. 2) to 5): Refer to Reference Example 1.

A three-week breeding test was conducted by freely ingesting water and feed. After the test was completed, the body weight gain, feed intake, and feed efficiency of each group of rats were calculated. The total lipid content and total cholesterol content were analyzed by a conventional method, and dissected to measure the weight of epididymal adipose tissue and liver tissue. Tables 2, 3 and 4 show the results.
Shown in In the glycolipid fraction-added group, the body weight gain was small and the feed efficiency was low in spite of the large intake of feed, compared to the group containing only soybean oil and the group added with lecithin (Table 2). The weight of the excreted feces was large, and the amounts of lipids and cholesterol excreted in the feces were larger than those in the other groups (Table 3). The weight of the epididymal adipose tissue and liver tissue was also significantly smaller (Table 4). From these results, it was clarified that the addition of a glycolipid fraction containing steryl glycoside and an acylated product thereof suppresses the accumulation of body fat and can prevent obesity.

[0022]

[Table 2] Note) Each value is shown as the mean ± standard error. Test sections with different symbols have a significant difference with a risk rate of 5% or less.

[0023]

[Table 3]

[0024]

[Table 4]

Reference Example 2 Preparation of Sesame Glycolipid Fraction and Concentrate Crude oil obtained by roasting and pressing sesame seeds by a conventional method was allowed to stand in a storage tank at 40 to 25 ° C. for 10 days. After filtering out the deposited precipitate (ori), 10 kg of this
Washing was repeated three times with 50 liters of ethanol at ６０60 ° C. Oil and fats and insolubles were removed, and ethanol was distilled off from the collected ethanol layer under reduced pressure to obtain 800 g of solids. This was dissolved in 5 liters of hexane, applied to a silica gel column (Wako gel C-100) in the same manner as described in Reference Example 1, and eluted with 2 liters of hexane (lecithin fraction), and further ethanol. It was divided into elution categories (glycolipid fraction, F3) when flowing down 15 liters. F3 was obtained in a yield of 600 g. As a result of composition analysis by high performance liquid chromatography, steryl glycoside 85 was obtained.
%, Acylated steryl glycoside 5%, 1,28-octacosadioic acid 8%, and other 2%.

Next, 500 g of F3 was dissolved in 5 liters of ethanol and applied to the same silica gel column, and the ethanol was allowed to flow down.
3-1 and F3-2 and F3-3). The solvent was distilled off from each section, the yield was measured, and the composition was analyzed. F3-1 was a 4 g yield, a glycolipid concentrate mainly containing 93% of acylated steryl glycoside, and F3-3 was a yield. 441 g, a glycolipid concentrate of 95% free steryl glycoside.

[Example 2] SD male rats of 4 weeks of age 7
The animals were grouped as one group. In the feed composition, the soybean oil-added group used in Example 1 shown in Table 1 was used as a control group, and 1% of this soybean oil was replaced with the same amount of other components shown below, and each was used as a test group. Glycolipid fraction addition section: glycolipid fraction F3 described in Reference Example 2, glycolipid concentrate (1) addition section: F3- containing acylated steryl glycoside described in Reference Example 2 as a main component
1. Glycolipid concentrate (2) added section: F3-3 containing steryl glycoside as described in Reference Example 2 as a main component.

In the same manner as in Example 1, water and feed were freely ingested and a three-week rearing test was carried out to determine the weight gain, feed intake and feed efficiency of the rats in each group, and the weight of liver and adipose tissue was measured. . The results are shown in Tables 5 and 6. Table 5 shows that when the glycolipid fraction and the concentrate were added to the feed, weight gain was suppressed and the feed efficiency was low.
From the results, it was confirmed that the weight of liver tissue and subcutaneous fat tissue was small, and it was clarified that it was effective in preventing obesity.

[0029]

[Table 5] Note) Each value is shown as the mean ± standard error. Test sections with different symbols have a significant difference with a risk rate of 5% or less. 1) The feed composition is the same as the soybean oil-added group in Table 1 2) 1% of glycolipid fraction F3 of Reference Example 2 is added 3) 1% of glycolipid concentrate F3-1 of Reference Example 2 is added 4) Reference 1% of the glycolipid concentrate F3-3 of Example 2 was added.

[0030]

[Table 6]

[0031]

According to the present invention, gum or odor generated in the process of producing oils and fats from general-purpose oil seeds such as soybeans and sesame is obtained by fractionating with a lower alcohol such as methanol or ethanol. And a glycolipid fraction containing the steryl glycoside and / or an acylated product thereof, or a concentrate thereof, as an active ingredient.
This anti-obesity agent can be used alone, or can be used as a food or drink, an animal feed or a pharmaceutical formulation by mixing with known raw materials, without requiring dietary restrictions, and without the risk of side effects, Easy to use.

Claims (4)

(57) [Claims] The present invention relates to a method wherein sterols derived from oil seeds and saccharides, which are obtained by fractionating gum or odor generated in a step of producing an oil or fat from oil seeds with a lower alcohol, are combined.
Steryl glycoside and its acylated product
An anti-obesity agent comprising a glycolipid containing as an active ingredient. 2. The agent for preventing obesity according to claim 1, wherein the oil seed is soybean or sesame. 3. The agent for preventing obesity according to claim 1, wherein the lower alcohol is methanol or ethanol. 4. The method according to claim 1, wherein the glycolipid is a sterol derived from oilseed.
The agent for preventing obesity according to any one of claims 1 to 3, which is a steryl glycoside and / or an acylated steryl glycoside bound to a saccharide .